PLus after the 10 year tax abatement the cash flow will be severly impacted2.

I'm so excited to hear the Maximizing Your Tax Benefits session!

How do you pay for the tax and insurance?

Being a real estate professional allows you to treat the income as non-passive, allowing higher high income tax payers to pay less in taxes.

I currently have a pre-tax retirement account with employer match and a Roth IRA invested in the stock market.

That doesn't seem right about having to chase your money - but would need a lot more info to provide a better opinion. also are you investing in one property and is your name secured or you giving an unsecured loan? 

The ultimate tax hit is at most $5k (20k * max 25% tax rate) and it's probably not worth it to 1031 exchange for that little of tax deferrals.

It’s all about securing the right agreements and understanding the rules. 

If we sense there is a red flag, were asking them to upload additional documents like tax returns w2's etc.

Almost every action taken in the economy is taxed and the faster the economy chugs forward the more taxes they collect.